3* The Willows Hotel

The Willows sits on a residential street in Lakeview, offering a quieter and more traditional base within reach of both Lincoln Park and Chicago’s Northalsted gay scene. It’s a smaller hotel with a cosy feel rather than a long list of facilities, and rooms have a classic style. Lake Michigan and Lincoln Park are nearby, while the bars around Northalsted can be reached on foot, although they’re not immediately outside the hotel. Downtown requires a short journey, but public transport links from Lakeview are good. GayMapper tip: a comfortable middle ground if you want to stay near the gay neighbourhood without being right in the thick of the nightlife.

The Peninsula is one of Chicago’s standout luxury hotels, just off Michigan Avenue in the heart of the Magnificent Mile. Rooms are spacious and polished, while the hotel has the kind of facilities you’d expect at this level, including an excellent spa, indoor swimming pool, restaurants and its well-known afternoon tea. The location is extremely convenient for shopping and many of Chicago’s central attractions, with the lakefront and Museum of Contemporary Art also nearby. Northalsted and Andersonville are several miles north, so this isn’t the place to stay specifically for gay nightlife. GayMapper tip: if you want full five-star luxury and sightseeing convenience, rather than gay bars outside the door, The Peninsula is hard to fault.

Viceroy Chicago combines five-star style with a Gold Coast location that feels a little more residential than the busiest parts of the Magnificent Mile. Rooms have a smart contemporary design, while the rooftop pool and bar are standout features during warmer months. Oak Street Beach, Michigan Avenue and some of Chicago’s best-known shopping and restaurants are all close by. As with the other Gold Coast hotels, the trade-off is distance from Northalsted and Andersonville, so you’ll need transport for the main gay nightlife. GayMapper tip: particularly appealing if you want modern luxury and a stylish rooftop scene while keeping Downtown Chicago firmly at the centre of the trip.

The Robey occupies a landmark Art Deco building right at the heart of Wicker Park, giving you a very different Chicago experience from the big hotels around the Magnificent Mile. Rooms combine modern design with the character of the original building, while the rooftop spaces are a highlight, offering impressive views back towards the Downtown skyline. Wicker Park itself is packed with restaurants, bars, cafés and independent shops, making it a great area for evenings closer to home. The main gay nightlife in Northalsted and Andersonville isn’t within walking distance, although transport connections are good. GayMapper tip: a strong choice if neighbourhood character, design and rooftop drinks matter more to you than staying close to the traditional gay scene.

Hotel Versey gives the familiar Days Inn brand a rather more colourful personality, with design inspired by Chicago’s music, art and neighbourhood culture. Its Lincoln Park location puts you between Downtown and Northalsted, so it can work particularly well if you want reasonably easy access to both sightseeing and gay nightlife without paying central Chicago prices. The bars around Northalsted aren’t immediately outside, but they’re within easy reach. Rooms are contemporary and informal, and there are plenty of restaurants and shops in the surrounding area. GayMapper tip: a useful value option if location matters more than luxury and you want to split your time between central Chicago and the gay scene.

The Drake is one of Chicago’s classic grand hotels, occupying a prominent position at the northern end of the Magnificent Mile close to Oak Street Beach and the Gold Coast. Expect traditional rather than cutting-edge luxury, with an imposing historic building, elegant public spaces and a real sense of old-school Chicago. The location is excellent for shopping, restaurants and central sightseeing, with the lakefront just outside. You’ll be well away from the main gay nightlife around Northalsted and Andersonville, so evenings out will involve a taxi, rideshare or public transport. GayMapper tip: choose The Drake for history, atmosphere and a prime central location rather than proximity to Chicago’s gay scene.